Methyl chloroformate → 2-Methoxycarbonylamino-2-phenyl-propionic acid

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Reaction Steps

To a solution of 2-Amino-2-phenyl-propionic acid (1.00 g, 6.06 mmol) in THF (17 mL), was added aqueous NaOH (6 M, 2.5 mL, 15.0 mmol) and Methyl Chloroformate (0.55 mL, 7.10 mmol). The solution was stirred for 18 h. Aqueous HCl (12 M, 1.5 mL, 18 mmol) was slowly added. The solution was diluted with HCl (1M) and extracted with Et2O (3 times). The combined organic layers were extracted with NaOH (2N, 3 times). The aqueous layers were acidified with HCl (12 N) and extracted with Et2O (3 times). The combined organic layers were dried over MgSO4 and concentrated. The crude oil was diluted in CH2Cl2 and concentrated again to provide 2-Methoxycarbonylamino-2-phenyl-propionic acid (0.66 g, 49%). LCMS-ESI+: calc'd for C11H13NO4: 223.08 (M+); Found: 223.97 (M+H+).

Provenance & Evidence